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Scientia Pharmaceutica is published by MDPI from Volume 84 Issue 3 (2015). Articles in this Issue were published by another publisher in Open Access under a CC-BY (or CC-BY-NC-ND) licence. Articles are hosted by MDPI on as a courtesy and upon agreement with Austrian Pharmaceutical Society (Österreichische Pharmazeutische Gesellschaft, ÖPhG).
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Sci. Pharm. 2013, 81(3), 793-806; (registering DOI)

Compounds from Gum Ammoniacum with Acetylcholinesterase Inhibitory Activity

Department of Pharmacognosy, University of Vienna, Althanstraße 14, 1090 Vienna, Austria
Institute of Organic Chemistry, University of Vienna, Währingerstraße 38, 1090 Vienna, Austria
Author to whom correspondence should be addressed.
Received: 28 June 2013 / Accepted: 12 August 2013 / Published: 12 August 2013
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The use of herbal medicinal preparations in dementia therapy has been studied based on experience from traditional medicine. A dichloromethane extract of gum ammoniacum, the gum-resin from Dorema ammoniacum D. Don had shown acetylcholinesterase (AChE) inhibitory activity in a previous study. The aim of this study was the isolation and characterization of the active compounds from this resin. The extract was investigated by a respective colorimetric microplate assay and the active zones were identified via TLC bioautography and isolated using several chromatographic techniques. The structures of the active components were characterized by one- and two-dimensional 1H and 13C NMR spectroscopy and mass spectrometry as (2'S,5'S)-2'-ethenyl-5'-(3-hy-droxy-6-methyl-4-oxohept-5-en-2-yl)-7-methoxy-2'-methyl-4H-spiro[chromene-3,1'-cyclopentane]-2,4-dione (1), which is an analogue of doremone A and a new natural compound, and as (2'S,5'R)-2'-ethenyl-5'-[(2R,4R)-4-hydroxy-6-methyl-3-oxohept-5-en-2-yl]-7-methoxy-2'-methyl-4H-spiro[chromene-3,1'-cyclo-pentane]-2,4-dione (2 = doremone A), (4E,8E)-1-(2,4-dihydroxyphenyl)-5,9,13-trimethyltetradeca-4,8,12-trien-1-one (3 = dshamirone), and 4,7-dihydroxy-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-2H-chromen-2-one (4 = am-moresinol). Dshamirone turned out to be the most active compound with an IC50 value for AChE inhibitory activity of 23.5 μM, whereas the other substances showed weak activity. The concentrations of the analytes in the resin were determined by HPLC as 3.1%, 4.6%, 1.9%, and 9.9%, respectively.
Keywords: Dorema ammoniacum; Acetylcholinesterase inhibition; Doremone A; Dshamirone; Ammoresinol; Spiro-sesquiterpenoidic chromane-2,4-dione Dorema ammoniacum; Acetylcholinesterase inhibition; Doremone A; Dshamirone; Ammoresinol; Spiro-sesquiterpenoidic chromane-2,4-dione
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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ADHAMI, H.-R.; LUTZ, J.; KÄHLIG, H.; ZEHL, M.; KRENN, L. Compounds from Gum Ammoniacum with Acetylcholinesterase Inhibitory Activity. Sci. Pharm. 2013, 81, 793-806.

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